JP2005222929A - Electroluminescent element - Google Patents
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本発明は、各種表示装置及び各種光源などとして広範囲に利用され、低い印加電圧で高輝度発光が可能で、かつ安定性にも優れた電界発光素子（ＥＬ素子）に関するものである。 The present invention relates to an electroluminescent element (EL element) which is widely used as various display devices and various light sources, and which can emit light with high luminance at a low applied voltage and has excellent stability.
ＥＬ素子は自己発光のために液晶素子にくらべて明るく、鮮明な表示が可能であるため古くから多くの研究者によって研究されてきた。現在実用レベルに達した発光素子としては無機蛍光体であるＺｎＳを用いた素子がある。しかし、このような無機のＥＬ素子は発光のための印加電圧として２００Ｖ以上が必要で広く使用されるには至っていない。 EL elements have been studied by many researchers for a long time because they are brighter and clearer than liquid crystal elements because of self-luminescence. As a light emitting element that has reached a practical level at present, there is an element using ZnS which is an inorganic phosphor. However, such an inorganic EL element requires 200 V or more as an applied voltage for light emission and has not been widely used.
これに対して有機材料を用いた電界発光素子は従来実用的なレベルからはほど遠いものであったが、１９８７年にコダック社のＣ．Ｗ．Ｔａｎｇらによって開発された積層構造素子によりその特性が飛躍的に進歩した。彼らは電子を輸送することの出来る有機蛍光体と、正孔を輸送することの出来る有機物を積層し、電子と正孔の両キャリヤーを蛍光体層中に注入して発光させることに成功した。これによって有機電界発光素子の発光効率が向上し、１０Ｖ以下の電圧で１０００ｃｄ／ｍ2 以上の発光が得られるようになった。その後多くの研究者によってその特性向上のための研究が行われ、現在では短時間の発光では１００００ｃｄ／ｍ2 以上の発光特性が得られている。 In contrast, an electroluminescent element using an organic material has been far from a practical level, but in 1987, Kodak's C.I. W. The characteristics of the multilayer structure element developed by Tang et al. They stacked organic phosphors capable of transporting electrons and organic materials capable of transporting holes, and succeeded in injecting both electron and hole carriers into the phosphor layer to emit light. As a result, the light emission efficiency of the organic electroluminescence device was improved, and light emission of 1000 cd / m 2 or more was obtained at a voltage of 10 V or less. Since then, many researchers have conducted research for improving the characteristics, and at present, emission characteristics of 10000 cd / m 2 or more are obtained in a short time emission.
しかし、このような従来の有機電界発光素子では、その基本的な発光特性はすでに十分実用範囲にあるが、実用化には至っていない。現在その実用化を妨げている最も大きな原因は、（１）駆動時の発光特性の長期安定性の不足、（２）長期保存安定性の不足、にある。ここで駆動時の劣化とは素子に電流を印加して駆動した時に発光輝度が低下したり、ダークスポットと呼ばれる発光しない領域が発生、成長したり、素子の短絡により破壊が起こったりする現象である。また、保存時の安定性とは作製した素子を長期保存しているだけでも発光特性が低下する現象である。本発明者らはこのような電界発光素子の発光の安定性、保存安定性に関する問題点を解決するためその劣化の機構を検討した。 However, such a conventional organic electroluminescent device has a basic light emission characteristic already in a practical range, but has not yet been put into practical use. At present, the biggest causes hindering its practical application are (1) lack of long-term stability of light emission characteristics during driving, and (2) lack of long-term storage stability. Here, deterioration during driving is a phenomenon in which light emission luminance decreases when a current is applied to the element, a non-light-emitting region called a dark spot is generated or grows, or destruction occurs due to a short circuit of the element. is there. In addition, the storage stability is a phenomenon in which the light emission characteristics are deteriorated even if the manufactured device is stored for a long time. The present inventors examined the mechanism of deterioration in order to solve the problems relating to the light emission stability and storage stability of the electroluminescent element.
その結果、特性劣化の大きな原因の一つがその発光材にあることが分かった。即ち、発光材として一般に利用されるトリス（８−ハイドロキシキノリン）アルミニウム（化４：略称Ａｌｑ３）のような発光材の蒸着薄膜は、（１）加熱したり電流を印加することにより変化して、膜形状が一様でなくなり、蛍光の発光効率が悪くなる、（２）空気中に保存しただけでも、湿度や酸素の影響で発光効率が悪くなる、などの変化を起こし、それによって素子の特性が著しく劣化することが分かった。湿度や酸素の影響は封止などの手段によりある程度防ぐことが出来るが、電流や温度による劣化は基本的にこのような手段により防ぐことは出来ない。 As a result, it was found that one of the major causes of characteristic deterioration is the light emitting material. That is, the deposited thin film of a light emitting material such as tris (8-hydroxyquinoline) aluminum (Chemical Formula 4: abbreviated as Alq3) generally used as a light emitting material is changed by (1) heating or applying a current, The film shape is not uniform, and the luminous efficiency of the fluorescence deteriorates. (2) Even if it is stored in the air, the luminous efficiency deteriorates due to the influence of humidity and oxygen. Was found to deteriorate significantly. The influence of humidity and oxygen can be prevented to some extent by means such as sealing, but deterioration due to current and temperature cannot basically be prevented by such means.
本発明は上記従来の課題を解決するもので、新しい電子輸送材料を提供し、発光の安定性と保存安定性に優れた電界発光素子を実現するものである。 The present invention solves the above-described conventional problems, and provides a new electron transport material, and realizes an electroluminescent device excellent in light emission stability and storage stability.
この目的を達成するために本発明の電界発光素子は、電圧を印加するための第１の電極と、正孔を発光層へ輸送する正孔輸送層と、電子と正孔により発光する発光層と、電子を発光層へ輸送する電子輸送層と、電圧を印加するための第２の電極とを有し、上記電子輸送層として、下記一般式（化５）で示される化合物、下記一般式（化６）で示される化合物、または下記一般式（化７）で示される化合物が用いられているものである。また、電圧を印加するための第１の電極と、正孔を発光層へ輸送する正孔輸送層と、電子を発光層へ輸送するとともに電子と正孔により発光する電子輸送層と、電圧を印加するための第２の電極とを有し、上記電子輸送層として、下記一般式（化５）で示される化合物、下記一般式（化６）で示される化合物、または下記一般式（化７）で示される化合物が発光材と混合して用いられているものである。 In order to achieve this object, the electroluminescent device of the present invention comprises a first electrode for applying a voltage, a hole transport layer for transporting holes to the light emitting layer, and a light emitting layer for emitting light by electrons and holes. And an electron transport layer for transporting electrons to the light emitting layer, and a second electrode for applying a voltage. As the electron transport layer, a compound represented by the following general formula (Formula 5), A compound represented by (Chemical formula 6) or a compound represented by the following general formula (Chemical formula 7) is used. A first electrode for applying a voltage; a hole transport layer that transports holes to the light-emitting layer; an electron transport layer that transports electrons to the light-emitting layer and emits light by electrons and holes; A compound represented by the following general formula (Formula 5), a compound represented by the following general formula (Formula 6), or the following general formula (Formula 7): ) Is used by mixing with a light emitting material.
ただし、（化５）の一般式で示されるアントラキノン誘導体における、ＲおよびＲ’はメチル基、エチル基、プロピル基、ブチル基、等のアルキル基、あるいはブトキシカルボニル基、ヘキシルカルボニル基、等のアルコキシカルボニル基、クロル基等のハロゲン、ニトロ基、シアノ基を示す。また（化６）の一般式で示されるインダンジオン誘導体における、Ｒ"の置換基はオルト、メタ、パラ位のいずれかの位置に置換した、メチル基、エチル基などのアルキル基、メトキシ基、エトキシ基、ブトキシ基などのアルコキシ基、ジエチルアミノ基、ジフェニルアミノ基、などのアルキルまたはアリールアミノ基、ニトロ基、シアノ基、トリフルオルメチル基、フルオル基、クロル基、カルボニル基、ブチルカルボニル基、フェニル基を示す。また（化７）の一般式で示されるインダンジオン誘導体における、Ａはパラフェニレン、メタフェニレン、１−ナフチル、２−ナフチル、１−アントリル、２−アントリル、スチリル、などのアリール基、あるいはアリーレン基である。むろん本発明はここに記載した各種の置換基に限定されるものではなく、蒸着などの方法によりすぐれた薄膜を形成し、かつそれらの薄膜が優れた電子輸送能力、熱や電気に対する安定性を有すれば同様に使用することが出来る。 However, R and R ′ in the anthraquinone derivative represented by the general formula of (Chemical Formula 5) are alkyl groups such as methyl group, ethyl group, propyl group, and butyl group, or alkoxy groups such as butoxycarbonyl group and hexylcarbonyl group. Halogen such as carbonyl group and chloro group, nitro group and cyano group are shown. In the indanedione derivative represented by the general formula of (Chem. 6), the substituent of R ″ is substituted at any position of ortho, meta, and para positions, such as an alkyl group such as a methyl group and an ethyl group, a methoxy group, Alkoxy or arylamino groups such as alkoxy group such as ethoxy group and butoxy group, diethylamino group and diphenylamino group, nitro group, cyano group, trifluoromethyl group, fluoro group, chloro group, carbonyl group, butylcarbonyl group, phenyl In the indanedione derivative represented by the general formula (7), A is an aryl group such as paraphenylene, metaphenylene, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, styryl, and the like. Of course, the present invention is limited to the various substituents described herein. It can be used in the same manner as long as an excellent thin film is formed by a method such as vapor deposition, and the thin film has an excellent electron transport ability and stability to heat and electricity.
以上のように本発明は、アントラキノン誘導体、インダンジオン誘導体を用いたことを特徴とする電界発光素子であり、本発明の材料を用いることにより、従来の電界発光素子の最も大きな課題であった発光寿命、保存安定性を格段に改良した電界発光素子を実現することが出来るものである。 As described above, the present invention is an electroluminescent element characterized by using an anthraquinone derivative and an indandione derivative, and by using the material of the present invention, light emission which has been the biggest problem of conventional electroluminescent elements. It is possible to realize an electroluminescent device with significantly improved lifespan and storage stability.
上記構成において、（化５）で記述されるアントラキノン化合物、または（化６）および（化７）で記述されるインダンジオン化合物は、優れた電子輸送能力を有しているばかりでなく熱的に安定で、蒸着により良好な薄膜を形成することができ、これらの電子輸送材の層を発光層と電極の間に設けた素子、あるいはこれらの電子輸送材と発光材を混合して用いた素子は、効率が良く、熱や電流に対して安定で、優れた発光特性、発光の安定性、及び保存安定性を実現することできる。 In the above structure, the anthraquinone compound described in (Chemical Formula 5) or the indandione compound described in (Chemical Formula 6) and (Chemical Formula 7) not only has an excellent electron transport capability, but also thermally. A stable, favorable thin film can be formed by vapor deposition, and an element in which a layer of these electron transport materials is provided between the light emitting layer and the electrode, or an element using a mixture of these electron transport materials and the light emitting material Is efficient, stable against heat and current, and can realize excellent light emission characteristics, light emission stability, and storage stability.
（実施例１）
以下、本発明の第１の実施例の電界発光素子の構成について、図面を用いて説明する。
(Example 1)
Hereinafter, the configuration of the electroluminescent element according to the first embodiment of the present invention will be described with reference to the drawings.
図１において、１１は本実施例の電界発光素子の基板となるガラス基板であり、１２は電圧印加するための透明電極であるＩＴＯ電極であり、１３は正孔を発光層１４へ輸送する正孔輸送層であり、１４は電子と正孔により発光する発光層であり、１５は電子を発光層１４へ輸送する電子輸送層であり、１６は電圧印加するための電極である。 In FIG. 1, reference numeral 11 denotes a glass substrate serving as a substrate of the electroluminescent element of this embodiment, 12 denotes an ITO electrode which is a transparent electrode for applying a voltage, and 13 denotes a positive electrode for transporting holes to the light emitting layer 14. A hole transport layer, 14 is a light emitting layer that emits light by electrons and holes, 15 is an electron transport layer that transports electrons to the light emitting layer 14, and 16 is an electrode for applying a voltage.
次に、本発明の第１の実施例の電界発光素子に用いる電子輸送材料の製造方法について説明する。 Next, the manufacturing method of the electron transport material used for the electroluminescent element of the 1st Example of this invention is demonstrated.
本実施例の電子輸送材料であるアントラキノン誘導体は以下の（化８）に従って合成した。 An anthraquinone derivative, which is an electron transport material of this example, was synthesized according to the following (Chemical Formula 8).
この化合物の同定は、元素分析、赤外測定により行い、さらに溶媒による再結晶法により精製し、純度を９９％以上とした。純度の確認はＴＬＣスキャナー、ＴＧ−ＤＴＡ、融点測定により行った。その結果融点、分解点の大きさが置換基により変化し、いくつかの置換基の場合には、融点、分解点が高い材料を得ることが出来た。以下にいくつかの代表的な合成化合物の融点（ｍｐ）、赤外吸収の位置（ｃｍ-1）の測定結果を（表１）に示す。ただし、（表１）に示したアントラキノン誘導体は次の一般式（化９）で示される構造を有している。 This compound was identified by elemental analysis and infrared measurement, and further purified by a recrystallization method using a solvent to obtain a purity of 99% or more. The purity was confirmed by TLC scanner, TG-DTA, and melting point measurement. As a result, the melting point and the size of the decomposition point varied depending on the substituent, and in the case of several substituents, a material having a high melting point and decomposition point could be obtained. The measurement results of melting points (mp) and infrared absorption positions (cm −1 ) of some typical synthetic compounds are shown in Table 1 below. However, the anthraquinone derivative shown in (Table 1) has a structure represented by the following general formula (Formula 9).
次に、本発明の第１の実施例の電界発光素子の製造方法について説明する。
十分に洗浄したＩＴＯ電極１２付きのガラス基板１１、正孔輸送層１３となる正孔輸送材としてテトラフェニルベンジジン化合物（（化１０）における置換基がＲ1＝m-ＣＨ3、Ｒ2＝Ｈ、Ｒ3＝Ｈ、である化合物）、発光層１４となる発光材として精製したアルミキノリン３量体（Ａｌｑ３）、電子輸送層１５となる電子輸送材としてアントラキノン誘導体（（表１）における化合物、１−１）、を蒸着装置にセットした。０．１ｎｍ／秒の速度で化合物を５０ｎｍの厚さで蒸着した。
Next, a method for manufacturing the electroluminescent element according to the first embodiment of the present invention will be described.
A glass substrate 11 with a sufficiently cleaned ITO electrode 12 and a tetraphenylbenzidine compound as a hole transport material to be a hole transport layer 13 (substituents in (Chemical Formula 10) are R1 = m-CH3, R2 = H, R3 = H), a purified aluminum quinoline trimer (Alq3) as a light emitting material to be the light emitting layer 14, an anthraquinone derivative (compound in (Table 1), 1-1) as an electron transporting material to be the electron transport layer 15 Were set in a vapor deposition apparatus. The compound was deposited with a thickness of 50 nm at a rate of 0.1 nm / sec.
なお膜厚は水晶振動子によってモニターした。Ａｌｑ３の蒸着は同じく０．１ｎｍ／秒の速度で行い、その膜厚は５０ｎｍとした。さらに化合物１−１を０．１ｎｍ／秒の速度で蒸着し、その厚さを５０ｎｍとした。最後にＭｇ／Ａｇ電極は０．４ｎｍ／秒の速度で行い、その厚さを１００ｎｍとした。これらの蒸着はいずれも真空を破らずに連続して行った。同様な手法でそれぞれアントラキノン誘導体（化合物１−２、１−３、１−４）についても素子を作製した。素子作製後、直ちに乾燥窒素中で電極の取り出しを行い、引続き素子の発光特性、発光寿命特性、保存安定性の試験を行った。得られた素子の発光特性は１００ｍＡ／ｃｍ2の電流を印加した場合の発光輝度で定義した。また、発光の安定性は２００ｃｄ／ｍ2の発光が得られる電流を連続で印加し、その時の発光輝度の変化を測定した。発光の寿命を輝度が半分の１００ｃｄ／ｍ2になるまでの時間と定義した。保存安定性は室温、乾燥窒素中に一定時間素子を放置後、２０ｍＡ／ｃｍ2の電流を印加し、輝度が初期発光特性の半分になるまでの時間で定義した。その結果を（表２）に示す。ただし、（表２）においてＡはテトラフェニルベンジジン化合物を示す。 The film thickness was monitored with a crystal resonator. The deposition of Alq3 was also performed at a rate of 0.1 nm / second, and the film thickness was 50 nm. Further, Compound 1-1 was deposited at a rate of 0.1 nm / second, and the thickness thereof was 50 nm. Finally, the Mg / Ag electrode was formed at a speed of 0.4 nm / second, and the thickness thereof was 100 nm. All of these depositions were performed continuously without breaking the vacuum. Devices were also prepared for anthraquinone derivatives (compounds 1-2, 1-3, and 1-4) in the same manner. Immediately after the device was fabricated, the electrode was taken out in dry nitrogen, and subsequently the device was tested for light emission characteristics, light emission lifetime characteristics, and storage stability. The light emission characteristics of the obtained device were defined as light emission luminance when a current of 100 mA / cm 2 was applied. The stability of light emission was measured by measuring the change in light emission luminance at that time by continuously applying a current at which light emission of 200 cd / m 2 was obtained. The lifetime of light emission was defined as the time until the luminance reached 100 cd / m 2 , which is half the luminance. The storage stability was defined as the time until the luminance became half of the initial light emission characteristics after applying the current of 20 mA / cm 2 after leaving the device in room temperature and dry nitrogen for a certain period of time. The results are shown in (Table 2). However, in Table 2, A represents a tetraphenylbenzidine compound.
比較のために同じ条件で本発実施例になる電子輸送層を設けない電界発光素子を作製しその特性を調べた。比較素子での発光特性、発光の寿命特性、保存安定性はそれぞれ、２２００ｃｄ／ｍ2、２２０Ｈｒ、４６０Ｈｒであった。このことから本実施例になるアントラキノン誘導体は発光寿命、保存安定性の向上に著しい効果があることが分かった。 For comparison, an electroluminescent device having no electron transport layer according to the present example was prepared under the same conditions, and the characteristics were examined. The light emitting characteristics, light emitting life characteristics, and storage stability of the comparative element were 2200 cd / m 2 , 220 Hr, and 460 Hr, respectively. From this, it was found that the anthraquinone derivative according to this example has a remarkable effect in improving the light emission lifetime and the storage stability.
なお、本実施例の電子輸送材料の評価の為に発光材としてＡｌｑ３を用いたが、むろんベリリウム−ベンゾキノリノール錯体等の各種の希土類錯体、オキサジアゾール誘導体、ポリパラフェニレンビニレンなどの各種の材料を用いることが出来る。また、各種キナクリドン誘導体、クマリン誘導体、ジシアノメチルピラン系誘導体、ルブレンなどのドーパントを添加することによりさらに高性能のＥＬを作製することが出来る。さらに正孔輸送材としても本実施例に示したテトラフェニルベンジジン誘導体以外に、トリールアミン系誘導体、ヒドラゾン系誘導体、ピラゾリン系誘導体、トリフェニルアミン系誘導体、オキサゾール系誘導体、ポリビニルカルバゾール、等を使用することが出来る。また、上部電極として本実施例で示したＭｇ／Ａｇ合金以外に、Ａｌ／Ｌｉ合金を用いることが出来、一般に発光効率は低下するがより安定な電極としてＡｌ電極を用いることが出来る。また、本実施例における電子輸送材料は単独で用いることも出来るが、２種類以上を共蒸着法などの方法で薄膜化して用いることもできる。 In addition, although Alq3 was used as a light-emitting material for the evaluation of the electron transport material of this example, various materials such as various rare earth complexes such as beryllium-benzoquinolinol complex, oxadiazole derivatives, polyparaphenylene vinylene, etc. Can be used. Further, by adding dopants such as various quinacridone derivatives, coumarin derivatives, dicyanomethylpyran derivatives, and rubrene, it is possible to produce higher performance EL. In addition to the tetraphenylbenzidine derivative shown in this example, a tolylamine derivative, a hydrazone derivative, a pyrazoline derivative, a triphenylamine derivative, an oxazole derivative, polyvinylcarbazole, etc. are used as the hole transport material. I can do it. In addition to the Mg / Ag alloy shown in the present embodiment, an Al / Li alloy can be used as the upper electrode. Generally, although the luminous efficiency is lowered, an Al electrode can be used as a more stable electrode. In addition, the electron transport material in this embodiment can be used alone, but two or more kinds can be used after being thinned by a method such as a co-evaporation method.
（実施例２）
以下、本発明の第２の実施例の電界発光素子の構成について、図面を用いて説明する。
(Example 2)
Hereinafter, the configuration of the electroluminescent element according to the second embodiment of the present invention will be described with reference to the drawings.
図２において、２１は本実施例の電界発光素子の基板となるガラス基板であり、２２は電圧印加するための透明電極であるＩＴＯ電極であり、２３は正孔を発光層兼電子輸送層２４へ輸送する正孔輸送層であり、２４は電子を輸送するとともに電子と正孔により発光する発光層兼電子輸送層であり、２５は電圧印加するための電極である。 In FIG. 2, 21 is a glass substrate which is a substrate of the electroluminescent element of this embodiment, 22 is an ITO electrode which is a transparent electrode for applying a voltage, and 23 is a light emitting layer / electron transport layer 24. 24 is a light emitting layer / electron transport layer that transports electrons and emits light by electrons and holes, and 25 is an electrode for applying a voltage.
本発明の第２の実施例の電界発光素子に用いる電子輸送材料の製造方法については第１の実施例と同様なので省略する。 Since the manufacturing method of the electron transport material used for the electroluminescent element of the second embodiment of the present invention is the same as that of the first embodiment, the description thereof is omitted.
次に、本発明の第２の実施例の電界発光素子の製造方法について説明する。
第１の実施例と同様の方法で、十分に洗浄したＩＴＯ電極２２付きのガラス基板２１、正孔輸送層２３となる正孔輸送材としてテトラフェニルベンジジン化合物（（化１０）における置換基が、Ｒ1＝m−ＣＨ3、Ｒ2＝Ｈ、Ｒ3＝Ｈである化合物）、発光層兼電子輸送層２４の一部となる発光材として精製したＡｌｑ３、発光層兼電子輸送層２４の一部となる電子輸送材としてアントラキノン誘導体（（表１）における化合物、１−１）、を蒸着装置にセットした。０．１ｎｍ／秒の速度で化合物を５０ｎｍの厚さで蒸着した。なお膜厚は水晶振動子によってモニターした。次にＡｌｑ３とアントラキノン誘導体１−１を共蒸着した。蒸着速度が０．２ｎｍ／秒となるように調節しその膜厚は５０ｎｍとした。最後にＭｇ／Ａｇ電極は０．４ｎｍ／秒の速度で行い、その厚さを１００ｎｍとした。これらの蒸着はいずれも真空を破らずに連続して行った。同様の手法でそれぞれアントラキノン誘導体（化合物１−２、１−３、１−４）についても素子を作製した。素子作製後、直ちに乾燥窒素中で電極の取り出しを行い、引続き素子の発光特性、発光寿命特性、保存安定性の試験を第１の実施例と同様の方法で行った。その結果を（表３）に示す。
Next, a method for manufacturing an electroluminescent element according to the second embodiment of the present invention will be described.
In the same manner as in the first embodiment, the glass substrate 21 with the ITO electrode 22 that has been sufficiently washed, the substituent in the tetraphenylbenzidine compound ((Chemical Formula 10)) as the hole transport material to be the hole transport layer 23, Compound in which R1 = m-CH3, R2 = H, R3 = H), purified Alq3 as a light emitting material that becomes a part of the light emitting layer / electron transport layer 24, and an electron that becomes a part of the light emitting layer / electron transport layer 24 An anthraquinone derivative (compound 1-1 in (Table 1)) as a transport material was set in a vapor deposition apparatus. The compound was deposited with a thickness of 50 nm at a rate of 0.1 nm / sec. The film thickness was monitored with a crystal resonator. Next, Alq3 and anthraquinone derivative 1-1 were co-evaporated. The deposition rate was adjusted to 0.2 nm / second and the film thickness was 50 nm. Finally, the Mg / Ag electrode was formed at a speed of 0.4 nm / second, and the thickness thereof was 100 nm. All of these depositions were performed continuously without breaking the vacuum. Devices were also prepared for anthraquinone derivatives (compounds 1-2, 1-3, and 1-4) in the same manner. Immediately after the device was fabricated, the electrode was taken out in dry nitrogen, and the light emission characteristics, light emission lifetime characteristics, and storage stability of the element were subsequently tested in the same manner as in the first example. The results are shown in (Table 3).
このことから本実施例になるアントラキノン誘導体はＡｌｑ３と共蒸着して用いても発光寿命、保存安定性の向上に著しい効果があることが分かった。 From this, it was found that the anthraquinone derivative according to the present example has a remarkable effect in improving the light emission life and the storage stability even when co-deposited with Alq3.
なお、本実施例の電子輸送材料の評価の為に発光材としてＡｌｑ３を用いたが、むろんベリリウム−ベンゾキノリノール錯体等の各種の希土類錯体、オキサジアゾール誘導体、ポリパラフェニレンビニレンなどの各種の材料を用いることが出来る。また、各種キナクリドン誘導体、クマリン誘導体、ジシアノメチルピラン系誘導体、ルブレンなどのドーパントを添加することによりさらに高性能のＥＬを作製することが出来る。さらに正孔輸送材としても本実施例に示したテトラフェニルベンジジン誘導体以外に、トリールアミン系誘導体、ヒドラゾン系誘導体、ピラゾリン系誘導体、トリフェニルアミン系誘導体、オキサゾール系誘導体、ポリビニルカルバゾール、等を使用することが出来る。また、上部電極として本実施例で示したＭｇ／Ａｇ合金以外に、Ａｌ／Ｌｉ合金を用いることが出来、一般に発光効率は低下するがより安定な電極としてＡｌ電極を用いることが出来る。また、本実施例における電子輸送材料は単独で用いることも出来るが、２種類以上を共蒸着法などの方法で薄膜化して用いることもできる。また、本実施例における電子輸送材とＡｌｑ３の比率は２０：１から１：２０の広範囲にわたって寿命特性に対して良好な影響を与える。 In addition, although Alq3 was used as a light-emitting material for the evaluation of the electron transport material of this example, various materials such as various rare earth complexes such as beryllium-benzoquinolinol complex, oxadiazole derivatives, polyparaphenylene vinylene, etc. Can be used. Further, by adding dopants such as various quinacridone derivatives, coumarin derivatives, dicyanomethylpyran derivatives, and rubrene, it is possible to produce higher performance EL. In addition to the tetraphenylbenzidine derivative shown in this example, a tolylamine derivative, a hydrazone derivative, a pyrazoline derivative, a triphenylamine derivative, an oxazole derivative, polyvinylcarbazole, etc. are used as the hole transport material. I can do it. In addition to the Mg / Ag alloy shown in the present embodiment, an Al / Li alloy can be used as the upper electrode. Generally, although the luminous efficiency is lowered, an Al electrode can be used as a more stable electrode. In addition, the electron transport material in this embodiment can be used alone, but two or more kinds can be used after being thinned by a method such as a co-evaporation method. In addition, the ratio of the electron transport material to Alq3 in this example has a good influence on the life characteristics over a wide range from 20: 1 to 1:20.
（実施例３）
以下、本発明の第３の実施例の電界発光素子について説明する。
(Example 3)
Hereinafter, an electroluminescent device according to a third embodiment of the present invention will be described.
本実施例の電界発光素子の構成は第１の実施例と同様なので省略する。
本実施例の電界発光素子に用いる電子輸送材料の製造方法について説明する。
Since the configuration of the electroluminescent element of this embodiment is the same as that of the first embodiment, a description thereof will be omitted.
The manufacturing method of the electron transport material used for the electroluminescent element of a present Example is demonstrated.
本実施例の電子輸送材料であるインダンジオン誘導体（化６）は以下の（化１１）に従って合成した。 The indandione derivative (Chemical formula 6), which is the electron transport material of this example, was synthesized according to the following chemical formula (11).
この化合物の同定は、元素分析、赤外測定により行い、さらに溶媒による再結晶法により精製し、純度を９９％以上とした。純度の確認はＴＬＣスキャナー、ＴＧ−ＤＴＡ、融点測定により行った。その結果融点、分解点の大きさが置換基により変化し、いくつかの置換基の場合には、融点、分解点が高い材料を得ることが出来た。以下にいくつかの代表的な合成化合物の融点（ｍｐ）、赤外吸収の位置（ｃｍ-1）の測定結果を（表４）に示す。 This compound was identified by elemental analysis and infrared measurement, and further purified by a recrystallization method using a solvent to obtain a purity of 99% or more. The purity was confirmed by TLC scanner, TG-DTA, and melting point measurement. As a result, the melting point and the size of the decomposition point varied depending on the substituent, and in the case of several substituents, a material having a high melting point and decomposition point could be obtained. The measurement results of melting points (mp) and infrared absorption positions (cm −1 ) of some typical synthetic compounds are shown in Table 4 below.
次に、本実施例の電界発光素子の製造方法について説明する。
本実施例の電界発光素子の製造方法は第１の実施例と同様の方法でインダンジオン誘導体（２−１〜２３）を電子輸送層として使用して作製した。得られた素子の特性を第１の実施例と同様の方法で評価した。その結果を（表５）に示す。
Next, a method for manufacturing the electroluminescent element of this example will be described.
The production method of the electroluminescent element of this example was produced by using the indandione derivative (2-1 to 23) as an electron transport layer in the same manner as in the first example. The characteristics of the obtained device were evaluated in the same manner as in the first example. The results are shown in (Table 5).
この結果から本実施例になるインダンジオン誘導体は発光寿命、保存安定性の改善に優れてた効果があることが分かった。 From these results, it was found that the indandione derivative of this example had an excellent effect in improving the light emission lifetime and storage stability.
なお、本実施例の電子輸送材料の評価の為に発光材としてＡｌｑ３を用いたが、むろんベリリウム−ベンゾキノリノール錯体等の各種の希土類錯体、オキサジアゾール誘導体、ポリパラフェニレンビニレンなどの各種の材料を用いることが出来る。また、各種キナクリドン誘導体、クマリン誘導体、ジシアノメチルピラン系誘導体、ルブレンなどのドーパントを添加することによりさらに高性能のＥＬを作製することが出来る。さらに正孔輸送材としても本実施例に示したテトラフェニルベンジジン誘導体以外に、トリールアミン系誘導体、ヒドラゾン系誘導体、ピラゾリン系誘導体、トリフェニルアミン系誘導体、オキサゾール系誘導体、ポリビニルカルバゾール、等を使用することが出来る。また、上部電極として本実施例で示したＭｇ／Ａｇ合金以外に、Ａｌ／Ｌｉ合金を用いることが出来、一般に発光効率は低下するがより安定な電極としてＡｌ電極を用いることが出来る。また、本実施例における電子輸送材料は単独で用いることも出来るが、２種類以上を共蒸着法などの方法で薄膜化して用いることもできる。 In addition, although Alq3 was used as a light-emitting material for the evaluation of the electron transport material of this example, various materials such as various rare earth complexes such as beryllium-benzoquinolinol complex, oxadiazole derivatives, polyparaphenylene vinylene, etc. Can be used. Further, by adding dopants such as various quinacridone derivatives, coumarin derivatives, dicyanomethylpyran derivatives, and rubrene, it is possible to produce higher performance EL. In addition to the tetraphenylbenzidine derivative shown in this example, a tolylamine derivative, a hydrazone derivative, a pyrazoline derivative, a triphenylamine derivative, an oxazole derivative, polyvinylcarbazole, etc. are used as the hole transport material. I can do it. In addition to the Mg / Ag alloy shown in the present embodiment, an Al / Li alloy can be used as the upper electrode. Generally, although the luminous efficiency is lowered, an Al electrode can be used as a more stable electrode. In addition, the electron transport material in this embodiment can be used alone, but two or more kinds can be used after being thinned by a method such as a co-evaporation method.
（実施例４）
以下、本発明の第４の実施例の電界発光素子について説明する。
Example 4
Hereinafter, an electroluminescent device according to a fourth embodiment of the present invention will be described.
本実施例の電界発光素子の構成は第２の実施例と同様なので省略する。
本実施例の電界発光素子に用いる電子輸送材料の製造方法は第３の実施例と同様なので省略する。
Since the configuration of the electroluminescent element of this example is the same as that of the second example, a description thereof will be omitted.
Since the manufacturing method of the electron transport material used for the electroluminescent element of this embodiment is the same as that of the third embodiment, the description thereof is omitted.
次に、本実施例の電界発光素子の製造方法について説明する。
本実施例の電界発光素子の製造方法は第２の実施例と同様の方法でインダンジオン誘導体（２−１〜２３）とＡｌｑ３の共蒸着層を発光・電子輸送層として使用して作製した。その素子の特性を第１の実施例と同様の方法で評価した。その結果を（表６）に示す。この結果から本実施例になるインダンジオン誘導体はＡｌｑ３と共蒸着して用いても発光寿命、保存安定性の改善に優れてた効果があることが分かった。
Next, a method for manufacturing the electroluminescent element of this example will be described.
The method for producing the electroluminescent element of this example was produced in the same manner as in the second example, using a co-deposited layer of indandione derivative (2-1 to 23) and Alq3 as the light emitting / electron transporting layer. The characteristics of the device were evaluated by the same method as in the first example. The results are shown in (Table 6). From these results, it was found that the indandione derivative according to this example had an excellent effect in improving the light emission life and storage stability even when co-deposited with Alq3.
なお、本実施例の電子輸送材料の評価の為に発光材としてＡｌｑ３を用いたが、むろんベリリウム−ベンゾキノリノール錯体等の各種の希土類錯体、オキサジアゾール誘導体、ポリパラフェニレンビニレンなどの各種の材料を用いることが出来る。また、各種キナクリドン誘導体、クマリン誘導体、ジシアノメチルピラン系誘導体、ルブレンなどのドーパントを添加することによりさらに高性能のＥＬを作製することが出来る。さらに正孔輸送材としても本実施例に示したテトラフェニルベンジジン誘導体以外に、トリールアミン系誘導体、ヒドラゾン系誘導体、ピラゾリン系誘導体、トリフェニルアミン系誘導体、オキサゾール系誘導体、ポリビニルカルバゾール、等を使用することが出来る。また、上部電極として本実施例で示したＭｇ／Ａｇ合金以外に、Ａｌ／Ｌｉ合金を用いることが出来、一般に発光効率は低下するがより安定な電極としてＡｌ電極を用いることが出来る。また、本実施例における電子輸送材料は単独で用いることも出来るが、２種類以上を共蒸着法などの方法で薄膜化して用いることもできる。また、本実施例における電子輸送材とＡｌｑ３の比率は２０：１から１：２０の広範囲にわたって寿命特性に対して良好な影響を与える。 In addition, although Alq3 was used as a light-emitting material for the evaluation of the electron transport material of this example, various materials such as various rare earth complexes such as beryllium-benzoquinolinol complex, oxadiazole derivatives, polyparaphenylene vinylene, etc. Can be used. Further, by adding dopants such as various quinacridone derivatives, coumarin derivatives, dicyanomethylpyran derivatives, and rubrene, it is possible to produce higher performance EL. In addition to the tetraphenylbenzidine derivative shown in this example, a tolylamine derivative, a hydrazone derivative, a pyrazoline derivative, a triphenylamine derivative, an oxazole derivative, polyvinylcarbazole, etc. are used as the hole transport material. I can do it. In addition to the Mg / Ag alloy shown in the present embodiment, an Al / Li alloy can be used as the upper electrode. Generally, although the luminous efficiency is lowered, an Al electrode can be used as a more stable electrode. In addition, the electron transport material in this embodiment can be used alone, but two or more kinds can be used after being thinned by a method such as a co-evaporation method. In addition, the ratio of the electron transport material to Alq3 in this example has a good influence on the life characteristics over a wide range from 20: 1 to 1:20.
（実施例５）
以下、本発明の第５の実施例の電界発光素子について説明する。
(Example 5)
Hereinafter, an electroluminescent device according to a fifth embodiment of the present invention will be described.
本実施例の電界発光素子の構成は第１の実施例と同様なので省略する。
本実施例の電界発光素子に用いる電子輸送材料の製造方法について説明する。
Since the configuration of the electroluminescent element of this embodiment is the same as that of the first embodiment, a description thereof will be omitted.
The manufacturing method of the electron transport material used for the electroluminescent element of a present Example is demonstrated.
本実施例の電子輸送材料であるインダンジオン誘導体（化７）は（化１１）に従って合成した。 The indandione derivative (Chemical Formula 7), which is the electron transport material of this example, was synthesized according to (Chemical Formula 11).
この化合物の同定は、元素分析、赤外測定により行い、さらに溶媒による再結晶法により精製し、純度を９９％以上とした。純度の確認はＴＬＣスキャナー、ＴＧ−ＤＴＡ、融点測定により行った。その結果融点、分解点の大きさが置換基により変化し、いくつかの置換基の場合には、融点、分解点が高い材料を得ることが出来た。以下にいくつかの代表的な合成化合物の融点（ｍｐ）、赤外吸収の位置（ｃｍ-1）の測定結果を（表７）に示す。 This compound was identified by elemental analysis and infrared measurement, and further purified by a recrystallization method using a solvent to obtain a purity of 99% or more. The purity was confirmed by TLC scanner, TG-DTA, and melting point measurement. As a result, the melting point and the size of the decomposition point varied depending on the substituent, and in the case of several substituents, a material having a high melting point and decomposition point could be obtained. The measurement results of melting points (mp) and infrared absorption positions (cm −1 ) of some typical synthetic compounds are shown in Table 7 below.
次に、本実施例の電界発光素子の製造方法について説明する。
本実施例の電界発光素子の製造方法は第１の実施例と同様の方法でインダンジオン誘導体（３−１〜４）を電子輸送層として使用して作製した。その特性を第１の実施例と同様の方法で評価した。その結果を（表８）に示す。この結果から本実施例になるインダンジオン誘導体は発光寿命、保存安定性の改善に優れてた効果があることが分かった。
Next, a method for manufacturing the electroluminescent element of this example will be described.
The method for producing the electroluminescent element of this example was produced by using the indandione derivative (3-1 to 4) as the electron transport layer in the same manner as in the first example. The characteristics were evaluated by the same method as in the first example. The results are shown in (Table 8). From these results, it was found that the indandione derivative of this example had an excellent effect in improving the light emission lifetime and storage stability.
なお、本実施例の電子輸送材料の評価の為に発光材としてＡｌｑ３を用いたが、むろんベリリウム−ベンゾキノリノール錯体等の各種の希土類錯体、オキサジアゾール誘導体、ポリパラフェニレンビニレンなどの各種の材料を用いることが出来る。また、各種キナクリドン誘導体、クマリン誘導体、ジシアノメチルピラン系誘導体、ルブレンなどのドーパントを添加すことによりさらに高性能のＥＬを作製することが出来る。さらに正孔輸送材としても本実施例に示したテトラフェニルベンジジン誘導体以外に、トリールアミン系誘導体、ヒドラゾン系誘導体、ピラゾリン系誘導体、トリフェニルアミン系誘導体、オキサゾール系誘導体、ポリビニルカルバゾール、等を使用することが出来る。また、上部電極として本実施例で示したＭｇ／Ａｇ合金以外に、Ａｌ／Ｌｉ合金を用いることが出来、一般に発光効率は低下するがより安定な電極としてＡｌ電極を用いることが出来る。また、本実施例における電子輸送材料は単独で用いることも出来るが、２種類以上を共蒸着法などの方法で薄膜化して用いることもできる。 In addition, although Alq3 was used as a light-emitting material for the evaluation of the electron transport material of this example, various materials such as various rare earth complexes such as beryllium-benzoquinolinol complex, oxadiazole derivatives, polyparaphenylene vinylene, etc. Can be used. Further, by adding dopants such as various quinacridone derivatives, coumarin derivatives, dicyanomethylpyran derivatives and rubrene, it is possible to produce higher performance EL. In addition to the tetraphenylbenzidine derivative shown in this example, a tolylamine derivative, a hydrazone derivative, a pyrazoline derivative, a triphenylamine derivative, an oxazole derivative, polyvinylcarbazole, etc. are used as the hole transport material. I can do it. In addition to the Mg / Ag alloy shown in the present embodiment, an Al / Li alloy can be used as the upper electrode. Generally, although the luminous efficiency is lowered, an Al electrode can be used as a more stable electrode. In addition, the electron transport material in this embodiment can be used alone, but two or more kinds can be used after being thinned by a method such as a co-evaporation method.
（実施例６）
以下、本発明の第６の実施例の電界発光素子について説明する。
(Example 6)
Hereinafter, an electroluminescent device according to a sixth embodiment of the present invention will be described.
本実施例の電界発光素子の構成は第２の実施例と同様なので省略する。
本実施例の電界発光素子に用いる電子輸送材料の製造方法は第５の実施例と同様なので省略する。
Since the configuration of the electroluminescent element of this example is the same as that of the second example, a description thereof will be omitted.
Since the manufacturing method of the electron transport material used for the electroluminescent element of this embodiment is the same as that of the fifth embodiment, the description thereof is omitted.
次に、本実施例の電界発光素子の製造方法について説明する。
本実施例の電界発光素子の製造方法は第２の実施例と同様の方法でインダンジオン誘導体（３−１〜４）とＡｌｑ３の共蒸着層を発光・電子輸送層として使用して作製した。その素子の特性を第１の実施例と同様の方法で評価した。その結果を（表９）に示す。この結果から本実施例になるインダンジオン誘導体はＡｌｑ３と共蒸着して用いても発光寿命、保存安定性の改善に優れてた効果があることが分かった。
Next, a method for manufacturing the electroluminescent element of this example will be described.
The electroluminescent element production method of this example was produced in the same manner as in the second example, using the co-deposited layer of indandione derivative (3-1 to 4) and Alq3 as the light emitting / electron transporting layer. The characteristics of the device were evaluated by the same method as in the first example. The results are shown in (Table 9). From these results, it was found that the indandione derivative according to this example had an excellent effect in improving the light emission life and storage stability even when co-deposited with Alq3.
なお、本実施例の電子輸送材料の評価の為に発光材としてＡｌｑ３を用いたが、むろんベリリウム−ベンゾキノリノール錯体等の各種の希土類錯体、オキサジアゾール誘導体、ポリパラフェニレンビニレンなどの各種の材料を用いることが出来る。また、各種キナクリドン誘導体、クマリン誘導体、ジシアノメチルピラン系誘導体、ルブレンなどのドーパントを添加することによりさらに高性能のＥＬを作製することが出来る。さらに正孔輸送材としても本実施例に示したテトラフェニルベンジジン誘導体以外に、トリールアミン系誘導体、ヒドラゾン系誘導体、ピラゾリン系誘導体、トリフェニルアミン系誘導体、オキサゾール系誘導体、ポリビニルカルバゾール、等を使用することが出来る。また、上部電極として本実施例で示したＭｇ／Ａｇ合金以外に、Ａｌ／Ｌｉ合金を用いることが出来、一般に発光効率は低下するがより安定な電極としてＡｌ電極を用いることが出来る。また、本実施例における電子輸送材料は単独で用いることも出来るが、２種類以上を共蒸着法などの方法で薄膜化して用いることもできる。また、本実施例における電子輸送材とＡｌｑ３の比率は２０：１から１：２０の広範囲にわたって寿命特性に対して良好な影響を与える。 In addition, although Alq3 was used as a light-emitting material for the evaluation of the electron transport material of this example, various materials such as various rare earth complexes such as beryllium-benzoquinolinol complex, oxadiazole derivatives, polyparaphenylene vinylene, etc. Can be used. Further, by adding dopants such as various quinacridone derivatives, coumarin derivatives, dicyanomethylpyran derivatives, and rubrene, it is possible to produce higher performance EL. In addition to the tetraphenylbenzidine derivative shown in this example, a tolylamine derivative, a hydrazone derivative, a pyrazoline derivative, a triphenylamine derivative, an oxazole derivative, polyvinylcarbazole, etc. are used as the hole transport material. I can do it. In addition to the Mg / Ag alloy shown in the present embodiment, an Al / Li alloy can be used as the upper electrode. Generally, although the luminous efficiency is lowered, an Al electrode can be used as a more stable electrode. In addition, the electron transport material in this embodiment can be used alone, but two or more kinds can be used after being thinned by a method such as a co-evaporation method. In addition, the ratio of the electron transport material to Alq3 in this example has a good influence on the life characteristics over a wide range from 20: 1 to 1:20.
（実施例７）
以下、本発明の第７の実施例の電界発光素子について説明する。
(Example 7)
Hereinafter, an electroluminescent device according to a seventh embodiment of the present invention will be described.
本実施例の電界発光素子の構成は第１の実施例と同様なので省略する。
本実施例の電界発光素子に用いる電子輸送材料の製造方法は第１の実施例、第３の実施例、及び第５の実施例と同様なので省略する。
Since the configuration of the electroluminescent element of this embodiment is the same as that of the first embodiment, a description thereof will be omitted.
Since the manufacturing method of the electron transport material used for the electroluminescent element of this example is the same as that of the first example, the third example, and the fifth example, the description thereof is omitted.
次に、本実施例の電界発光素子の製造方法について説明する。
本実施例の電界発光素子の製造方法は第１の実施例と同様の方法でアントラキノン誘導体１−２、インダンジオン誘導体２−１５、インダンジオン誘導体３−１を電子輸送層として用い、その電子輸送層の厚さを変えて素子を作製した。その素子の特性を第１の実施例と同様の方法で評価した。その結果を（表１０）に示す。この結果から本実施例に成る電子輸送層は５ｎｍ以上の厚さで有効で２０〜５０ｎｍの範囲が最適であり、２００ｎｍ以上の厚さは発光効率に悪い影響があることが分かった。
Next, a method for manufacturing the electroluminescent element of this example will be described.
The manufacturing method of the electroluminescent element of this example is the same as that of the first example, using anthraquinone derivative 1-2, indandione derivative 2-15, and indandione derivative 3-1 as the electron transport layer, and its electron transport. Devices were fabricated by changing the layer thickness. The characteristics of the device were evaluated by the same method as in the first example. The results are shown in (Table 10). From this result, it was found that the electron transport layer according to the present example is effective at a thickness of 5 nm or more and optimally in a range of 20 to 50 nm, and a thickness of 200 nm or more has a bad influence on the light emission efficiency.
なお、本実施例の電子輸送材料の評価の為に発光材としてＡｌｑ３を用いたが、むろんベリリウム−ベンゾキノリノール錯体等の各種の希土類錯体、オキサジアゾール誘導体、ポリパラフェニレンビニレンなどの各種の材料を用いることが出来る。また、各種キナクリドン誘導体、クマリン誘導体、ジシアノメチルピラン系誘導体、ルブレンなどのドーパントを添加することによりさらに高性能のＥＬを作製することが出来る。さらに正孔輸送材としても本実施例に示したテトラフェニルベンジジン誘導体以外に、トリールアミン系誘導体、ヒドラゾン系誘導体、ピラゾリン系誘導体、トリフェニルアミン系誘導体、オキサゾール系誘導体、ポリビニルカルバゾール、等を使用することが出来る。また、上部電極として本実施例で示したＭｇ／Ａｇ合金以外に、Ａｌ／Ｌｉ合金を用いることが出来、一般に発光効率は低下するがより安定な電極としてＡｌ電極を用いることが出来る。また、本実施例における電子輸送材料は単独で用いることも出来るが、２種類以上を共蒸着法などの方法で薄膜化して用いることもできる。 In addition, although Alq3 was used as a light-emitting material for the evaluation of the electron transport material of this example, various materials such as various rare earth complexes such as beryllium-benzoquinolinol complex, oxadiazole derivatives, polyparaphenylene vinylene, etc. Can be used. Further, by adding dopants such as various quinacridone derivatives, coumarin derivatives, dicyanomethylpyran derivatives, and rubrene, it is possible to produce higher performance EL. In addition to the tetraphenylbenzidine derivative shown in this example, a tolylamine derivative, a hydrazone derivative, a pyrazoline derivative, a triphenylamine derivative, an oxazole derivative, polyvinylcarbazole, etc. are used as the hole transport material. I can do it. In addition to the Mg / Ag alloy shown in the present embodiment, an Al / Li alloy can be used as the upper electrode. Generally, although the luminous efficiency is lowered, an Al electrode can be used as a more stable electrode. In addition, the electron transport material in this embodiment can be used alone, but two or more kinds can be used after being thinned by a method such as a co-evaporation method.
１１、２１ ガラス基板
１２、２２ ＩＴＯ電極
１３、２３ 正孔輸送層
１４ 発光層
１５ 電子輸送層
１６、２５ 電極
２４ 発光層兼電子輸送層
DESCRIPTION OF SYMBOLS 11, 21 Glass substrate 12, 22 ITO electrode 13, 23 Hole transport layer 14 Light emitting layer 15 Electron transport layer 16, 25 Electrode 24 Light emitting layer and electron transport layer
Claims (6)
ここで、Ａはパラフェニレン、メタフェニレン、１−ナフチル、２−ナフチル、１−アントリル、２−アントリル、スチリル、などのアリール基、あるいはアリーレン基である。 An electroluminescent device using an indandione compound represented by the following general formula. However, A shows a substituent and n shows 1 or 2.
Here, A is an aryl group such as paraphenylene, metaphenylene, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, styryl, or an arylene group.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| KR20120029096A (en) * | 2010-09-16 | 2012-03-26 | 엘지디스플레이 주식회사 | Quantum-dot light emitting diode and method for fabrication the same |
| KR101163032B1 (en) | 2009-11-23 | 2012-07-09 | 충남대학교산학협력단 | Triphenylamin derivative electro luminescent dye and its preparation method |
| CN109851571A (en) * | 2019-01-21 | 2019-06-07 | 浙江大学 | A kind of organic photovoltaic cell being conjugated small organic molecule modifying interface material, preparation method and its composition |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| KR101163032B1 (en) | 2009-11-23 | 2012-07-09 | 충남대학교산학협력단 | Triphenylamin derivative electro luminescent dye and its preparation method |
| KR20120029096A (en) * | 2010-09-16 | 2012-03-26 | 엘지디스플레이 주식회사 | Quantum-dot light emitting diode and method for fabrication the same |
| KR101686107B1 (en) | 2010-09-16 | 2016-12-13 | 엘지디스플레이 주식회사 | Quantum-dot light emitting diode and method for fabrication the same |
| CN109851571A (en) * | 2019-01-21 | 2019-06-07 | 浙江大学 | A kind of organic photovoltaic cell being conjugated small organic molecule modifying interface material, preparation method and its composition |
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